Singer was born in Allegheny City, Pennsylvania. As a young man he worked for his father's steel company, located in nearby Pittsburgh. Following the company's merger in 1900, Singer decided to pursue a full-time career as a painter. In 1901 he traveled to Paris, where he briefly entered the atelier of Jean-Paul Laurens and attended classes at the Academie Julian. By the end of 1901, Singer and his wife had settled in the artists colony of Laren, Holland. Three years later Singer traveled to Norway, and over the next ten years he split his time living in Holland, and Olden, Norway, a remote fishing village in the Nordfjord. At the beginning of World War I, Singer permanently settled in Olden.
Singer exhibited his Norwegian landscapes widely in the United States and Europe. The first large scale exhibition of these works was held in 1923 at the Frans Buffa & Sons Gallery in Amsterdam. In 1927, Singer founded an art and cultural center in his wifes hometown of Hagerstown, Maryland. The center, known today as the Washington County Museum of Fine Arts, opened in 1931. Singer's paintings are found in numerous museum collections, including the Washington County Museum of Fine Arts, the Art Institute of Chicago, and the Pennsylvania Academy of the Fine Arts. Singer's former home in Laren is now known as the Singer Museum. It includes work by the artist as well as of Dutch artists of the period 1880-1950.
"A Winter Night" was painted in Norway in 1921. From the time of his first visit to the country, Singer was overwhelmed by the majestic beauty of its mountain scenery, which he often pictured under a blanket of snow. In his Norwegian paintings, Singer was concerned above all with expressing the spiritual essence of the landscape, which he viewed as reflective of the mystery, power and blessing of the Deity. As William H. Gerdts has noted, Singer focused on the great mountain peaks which rise up in glory, sometimes almost spectral images in the background, sometimes in full clarity, but always harmonious elements of the whole landscape. They might be thought of as paternal overseers, never threatening or ominous ("Some Thoughts on the Painting of William H. Singer, Jr., essay in William H. Singer, Jr."[1868-1943] [Hagerstown, Maryland: Washington Country Museum of Fine Arts, 1981], p. 16).
Singers Norwegian paintings recall the Symbolist landscapes of the Italo-Swiss painter Giovanni Segantini. Both artists specialized in painting mountain scenery, emphasized patterns found in nature, and employed the prismatic color of Impressionism. Frederic Fairchild Sherman noted that with calculated skill [Singer] builds the majesty of the mountains to emphasize the transitory loveliness of the starlight in a canvas like "A Winter Night", and by means of a foreground of relative intimacy brings it close to the spectator. Indeed, the foreground is consciously exploited in his canvases and serves a real need with telling effect. He never allows it to become commonplace and its varied character is in keeping with what it introduced, whether an almost Oriental tracery of tree forms, silvery with snow against the frozen hills, or a misty halloed moonlight in the silence of the North (Norwegian Landscapes by William H. Singer, Jr., Art in America and Elsewhere 17 [December 1928]: 55).